The Master of 1499 diptych has paintings on both sides of both panels, all originally from the hand of a single artist whose name is unknown but whose nickname derives from this diptych, which is dated 1499. This artist's distinctive style is recognized in at least one other diptych, the Angel Gabriel and Virgin Annunciate. Another artist later added a second portrait to the reverse of the original donor portrait, leaving some of the original marbling visible in the background.

The primary images depict the Virgin and Child in a Gothic church and the Cistercian abbot Christiaan de Hondt in prayer. The Virgin is very large relative to the architecture in order to emphasize her role as the personification of the Church. This image is a copy of a famous painting by Jan van Eyck, Virgin in the Church (Staatliche Museen zu Berlin, Gemäldegalerie). The Master of 1499 may have known that work from a print or drawing, for his rendering is more linear and decorative than Van Eyck's painting, and the colors of the Virgin's garments are different.

From 1495 to 1509 Christiaan de Hondt was the abbot at Ter Duinen, a Cistercian abbey not far from Bruges. He is shown here in his well-furnished bed chamber, warmed by a fire and surrounded by the trappings of his office. He kneels before his prie-dieu (prayer desk), in adoration before the Virgin and Child on the facing panel.

The exterior of the diptych includes a portrait of Robrecht de Clercq on one panel and a hieratic image of Christ as Salvator Mundi (savior of the world) on the other panel. De Clercq served as the abbot of Ter Duinen between 1519 and 1557 and was thus a successor to De Hondt.